1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 520698Notes

Reaction equation

[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)=[CH:4][CH:3]=1.[CH3:16][N:17]1[C:21]([CH3:22])=[C:20]([C:23](O)=[O:24])[C:19](=[O:26])[N:18]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[NH2:13][C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([NH:1][C:23]([C:20]3[C:19](=[O:26])[N:18]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:17]([CH3:16])[C:21]=3[CH3:22])=[O:24])=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 4-(4-aminophenoxy)pyridin-2-amine (101 mg, 0.5 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (118 mg, 0.51 mmol) in DCM (5 mL) was added EDCI (115 mg, 0.6 mmol) and HOAT (13.6 mg, 0.1 mmol). The reaction was stirred at 45° C. for 3 hours, and then quenched with water (20 mL). The organic phase was separated and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=20/1) to give the title compound as a light grey solid (110 mg, 49.2%).

Workup

customquenched with water (20 mL)
customThe organic phase was separated
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=20/1)

Sources & evidence

ORD record: ord-c3d8185e6f914b71bc3d284cc4854abf
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326975B2

Reaction notes

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